~snip
You didn't say which jurisdiction you are in.
I assumed you live in Ontario due to advice you gave me several years ago about a lake in the Orillia region.
Are you multi-jurisdictional? I know if you're a USA citizen they'll chase you all over the world for taxes. Does that apply to dual citizenship?
While I have the option, I decided long ago not to pursue US citizenship. My biggest concern was having to register for the draft but the tax code in the US is insanely complex and one of the hoops to jump through in order to get my citizenship was to file the 10 previous years of income tax forms. In my mind, it wouldn't make sense to pursue it unless I were to take up residence there on a permanent basis and I was already comfortable here.
A friend of my sister is currently going through the process of renouncing her US citizenship and it involves an interview and a hefty processing fee. She's got a business in Canada and she's been paying US federal income tax every year - she has dual citizenship. I don't know the specifics of her case but there is a tax treaty between Canada and the US which prevents double taxation on your income so my mom never paid a dime in US taxes while she lived and worked here as a permanent resident. I guess the difference is employment vs self-employment.
Being US citizen is a fucking mess when you are REALLY wealthy and 'global' citizen. You don't choose where you are born, but the (VERY agressive) tax system has nothing to envy of the communists countries...